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首页> 外文学位 >Characterization of the separation of paclitaxel and related taxanes by reversed phase liquid chromatography on hydrocarbonaceous and fluorinated stationary phases.
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Characterization of the separation of paclitaxel and related taxanes by reversed phase liquid chromatography on hydrocarbonaceous and fluorinated stationary phases.

机译：反相液相色谱法在烃和氟化固定相上分离紫杉醇和相关紫杉烷的特征。

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摘要

Fluorinated columns have been reported to exhibit superior selectivity in the separation of taxanes. This study investigates the differences between fluorinated and hydrocarbonaceous stationary phases in the separation of taxanes and in reversed phase liquid chromatography in general. In this context the phenomenon of changes of elution order with variation of mobile phase composition and temperature is considered as well. Propyl-perfluorophenyl, ethyl-perfluorohexyl and ethyl-perfluoro (1-dimethyl-heptyl) phases are characterized in their selectivity to various compounds and compared to a regular hydrocarbonaceous octyl phase.; Using mobile phase and temperature optimization baseline separation of 15 taxanes is achieved on all phases in 9.5 to 23 minutes in aqueous acetonitrile. The fluorinated columns do not show any definite advantage in the separation of taxanes or other model compounds including aromatic and non-aromatic structures with various functional groups.; Xylosyl-taxol compounds exhibit increasing retention with increasing temperature at mobile phase compositions around 50% acetonitrile leading to exchanges of elution order with other taxanes. The effect slowly vanishes with increasing or decreasing concentration of acetonitrile. This aberrant temperature behavior is shown to be the caused by hydroxyl groups bound to non-aromatic backbone structures and is proportionally dependent on molecular size and degree of hydroxylation of the solute.; Taxanes, especially xylosyl taxol compounds, are found to show initially decreasing retention upon addition of water to the mobile phase followed by the usually observed increasing retention. At higher water concentrations the retention of xylosyl taxol compounds increases much more sharply compared to the other taxanes leading to multiple exchanges of elution order. The initial decrease of retention is attributed to hydroxyl group interactions and is independent of the aromatic or non-aromatic nature of the backbone structure. The increase of retention with further increase in the water concentration is shown to depend on the molecular size of the carbon backbone structure.; A model based on the preferential solvation of the solute is proposed to explain the mechanism of the effects stated above. The retention of the solute does not depend on the chemical structure of the solute but on the structure of a solute-solvent complex. The composition of this complex changes with temperature and mobile phase composition affecting retention of the solute.
机译：据报道，氟化柱在紫杉烷的分离中显示出优异的选择性。这项研究调查了紫杉烷分离和反相液相色谱中氟化和烃质固定相之间的差异。在这种情况下，还考虑了洗脱顺序随流动相组成和温度变化而变化的现象。丙基全氟苯基，乙基全氟己基和乙基全氟（1-二甲基庚基）相的特征在于它们对各种化合物的选择性，并与常规的烃辛基相进行了比较。使用流动相和温度优化，可以在9.5至23分钟内在乙腈水溶液中在所有相上实现15种紫杉烷的基线分离。氟化柱在紫杉烷类或其他模型化合物（包括具有各种官能团的芳族和非芳族结构）的分离中未显示任何明确的优势。木糖基紫杉醇化合物在约50％乙腈的流动相组合物中随温度升高而显示出更高的保留力，从而导致洗脱顺序与其他紫杉烷类交换。随着乙腈浓度的增加或减少，该作用逐渐消失。该异常的温度行为被证明是由与非芳族骨架结构键合的羟基引起的，并且成比例地取决于分子大小和溶质的羟基化程度。发现在向流动相中加水后，紫杉烷类化合物，特别是木糖基紫杉醇化合物，最初显示出保留率降低，然后通常观察到保留率提高。在较高的水浓度下，与其他紫杉烷类化合物相比，木糖基紫杉醇类化合物的保留量增加得多，从而导致洗脱顺序的多次交换。保留的初始降低归因于羟基相互作用，并且与骨架结构的芳族或非芳族性质无关。随着水浓度的进一步增加，保留量的增加显示出取决于碳骨架结构的分子大小。提出了基于溶质优先溶剂化的模型来解释上述作用机理。溶质的保留不取决于溶质的化学结构，而是取决于溶质-溶剂配合物的结构。该配合物的组成随温度和流动相组成而变化，从而影响溶质的保留。

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  • 作者

    Dolfinger, Ralf.;

  • 作者单位

    City University of New York.;

  • 授予单位 City University of New York.;
  • 学科 Chemistry Analytical.; Chemistry Pharmaceutical.
  • 学位 Ph.D.
  • 年度 2003
  • 页码 230 p.
  • 总页数 230
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;药物化学;
  • 关键词

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